3'-Hydroxyphenylacetic acid → HCID 68676419、化合物

HRID 1994067ノート

反応式

HRID 1994067 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:13][O:14][C:15](=[O:21])[C@@H:16]1[CH2:20][CH2:19][CH2:18][NH:17]1.ON1C2C=CC=C[C:26]=2N=N1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:13]([O:14][C:15]([C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)=[O:21])[CH3:26]

参加物

8

反応物 4

HCID 121223'-Hydroxyphenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733200methyl L-prolinate hydrochloride

生成物 1

HCID 68676419HCID 68676419、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 3-hydroxy phenylacetic acid (1.52 g, 10.0 mmol) in 10 mL of DCM is added L-proline methyl ester hydrochloride (1.80 g, 10.0 mmol) followed by the addition of TEA (1.67 mL, 12 mmol), 1-hydroxybenzotriazole (HOBt, 1.17 g, 10 mmol), and EDCl (1.92 g, 10 mmol). The mixture is stirred at RT for 4 days. Ethyl acetate and water is added, and the organic layer is separated and washed with brine, dried over anhydrous sodium sulfate, and concentrated. The crude mixture is purified by flash chromatography (silica gel) eluting with hexane:ethyl acetate (1:2) to give (R)-1-[2-(3-hydroxy-phenyl)-acetyl]-pyrrolidine-2-carboxylic acid ethyl ester as an oil.

後処理

  1. customthe organic layer is separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude mixture is purified by flash chromatography (silica gel)
  6. washeluting with hexane:ethyl acetate (1:2)

出典と根拠

ORDレコード
ord-9758474a3e87468f8c1706c1219c0e6e
出典データセット
uspto-grants-2010_01
特許番号
US07652061B2

反応ノート

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